Pineland Vacations from $390

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Your Pineland Vacation

Say bye-bye to the worries of planning and hello to a Pineland vacation package. With everything organized before you go, you can focus on discovering the best of this city, starting with North Captiva, which is good for watersports, cycling and coastal beaches. Ready to venture out and explore? Calusa Heritage Trail, Randell Research Center and Useppa Museum are just three of the best places to visit during your trip to Pineland. No matter your travel plans or the size of your budget, putting together a tailored Pineland vacation is a piece of cake with Expedia.

The Latest Pineland vacation packages

Price found within the past 48 hours. Click for updated prices.
Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

Sunseeker Resort Florida Gulf Coast, Curio Collection Hilton

4 out of 5
Save 100% on your flight
Price was $599, price is now $390 per person
$390
per person
Mar 25 - Mar 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
9.2/10 Wonderful! (1,612 reviews)
The hotel was well kept, and very clean

Reviewed on Jan 12, 2026

3583 Cape Haze Drive Unit c

3583 Cape Haze Drive Unit c

3.5 out of 5
Price was $1,835, price is now $1,714 per person
$1,714
per person
Feb 12 - Feb 19
found 14 hours ago
Roundtrip flight included
New York (JFK) to Punta Gorda Airport (PGD)
No reviews
Knights Inn Port Charlotte

Knights Inn Port Charlotte

2 out of 5
Price was $395, price is now $395 per person
$395
per person
Mar 16 - Mar 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Punta Gorda Airport (PGD)
5.8/10 (425 reviews)
It was clean, towels and soap shampoo provided. Bed was comfortable

Reviewed on Aug 27, 2025

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Discover the most popular places to visit in Pineland

Koucky Gardens & Gallery

You can spend time exploring the galleries in Koucky Gardens & Gallery in Pine Island Center. Wander the beautiful beaches and marina in this family-friendly area.

Koucky Gardens & Gallery

Goodwins Island

Commune with nature and explore the great outdoors at Goodwins Island during your travels in Bokeelia. Take in the museums while you're in the area.

Goodwins Island

Randell Research Center

You can spend time exploring the galleries in Randell Research Center during your travels in Pineland. Wander the beautiful beaches and marina in this family-friendly area.

Randell Research Center

What to do in Pineland

Close-up encounters with our beautiful Dolphins

Private Dolphin & Sightseeing Boat Day Tour

$185
per adult
Private Dolphin & Sightseeing Boat Day Tour
Guests having fun

4 hours Private Eco Boat Tour Wildlife and Nature in Pine Island

$800
per traveler
4 hours Private Eco Boat Tour Wildlife and Nature in Pine Island
See all activities in Pineland

Pineland Hotel Deals

Lani Kai Beachfront Resort

Lani Kai Beachfront Resort

3.5 out of 5
1400 Estero Blvd Fort Myers Beach FL
Fully refundableReserve now, pay when you stay
$186 nightly
The price is $208 total per night from Jan 14 to Jan 15
$208 total
Jan 14 - Jan 15
Total with taxes and fees
9/10 Wonderful! (1,097 reviews)
Great location, fun atmosphere lots of fun amenities!

Reviewed on Jan 11, 2026

Lani Kai Beachfront Resort
Marriott Sanibel Harbour Resort & Spa

Marriott Sanibel Harbour Resort & Spa

4 out of 5
17260 Harbour Pointe Dr Fort Myers FL
Fully refundableReserve now, pay when you stay
$391 nightly
The price is $436 total per night from Jan 14 to Jan 15
$436 total
Jan 14 - Jan 15
Total with taxes and fees
8.4/10 Very Good! (1,000 reviews)
Staff was very nice. A problem we had was their were 4 of us in the room and trying to get 4 towels and washcloths was a hard task, also coffee in room.

Reviewed on Jan 3, 2026

Marriott Sanibel Harbour Resort & Spa
Holiday Inn Express Cape Coral-Fort Myers Area by IHG

Holiday Inn Express Cape Coral-Fort Myers Area by IHG

2.5 out of 5
1538 Cape Coral Pkwy E Cape Coral FL
Fully refundable
$170 nightly
The price is $190 total per night from Jan 18 to Jan 19
$190 total
Jan 18 - Jan 19
Total with taxes and fees
9.2/10 Wonderful! (1,159 reviews)
Dry nice

Reviewed on Jan 11, 2026

Holiday Inn Express Cape Coral-Fort Myers Area by IHG
See all 13,372 properties in Pineland
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Find the Best Pineland Vacation Packages

Pineland Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Southwest Florida Intl. Airport (RSW)
Top Sights
Museum of the Islands, Useppa Museum and Calusa Heritage Trail

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Frequently asked questions

How much does a Pineland vacation package cost?
You can grab a vacation package to this popular destination from $390 on Expedia. However, how much your vacation to Pineland costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Pineland?
If you'd like to score a cheap Pineland vacation package, consider planning a trip in September, October and December. You'll typically find lower rates on airfares and hotels during these months — ideal for a budget-friendly getaway.
How many days is enough for Pineland?
The ideal length for your Pineland vacation depends on what you'd like to do. Usually, a few days to a week will give you time to visit all the leading sights and discover some hidden treasures along the way.
How to find the best Pineland package deals?
Use Expedia's filter tool to help you find some terrific Pineland package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Pineland package deals in the low season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book a Pineland vacation as a package?
You can enjoy significant savings on your Pineland escape by booking a personalized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Pineland?
If you have your Pineland travel dates finalized, book as soon as you can to snap up some incredible deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Pineland?

  1. Choose when to go: Check your schedule and get packing. Your favorite time of year and the activities on offer will also help you decide when to escape to Pineland.
  2. Figure out your budget: Ensure you have enough money to pay for everything from meals and transportation to flights and experiences. Your accommodations will probably be the largest expense during your trip to Pineland.
  3. Explore Pineland with our trip planning tool: Gain insights into the leading attractions and best hotels for your trip to Pineland. You can also save your must-visit places, collaborate with friends and family and organize all your plans in one place.
  4. Determine how many days away: Start by compiling a list of the attractions and activities you want to get to in Pineland. Then, estimate how long you'll need at each, along with any travel time.
  5. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Pineland vacation package that brings all your bookings together.
  6. Book any activities or excursions: Here's the fun part — locking in everything you want to see and do. Check out some of the exciting things to do in Pineland in Pineland and reserve your tickets early to save time (and maybe some cash too!).

Does Expedia offer Book Now, Pay Later Pineland vacation packages?
Secure your ideal getaway to Pineland with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for your next payday — we've teamed up with online lender Affirm to give you more flexibility with your finances. Our vacation packages with payment plans mean you can spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's easy to stick to your budget and snap up bargains before they sell out.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.